top of page
Ashley2- Logo.png

13 Restaurants Worth Trying in Chicago (Part 2)

Updated: Oct 25, 2023

It’s been a while, and things are heating up in Chicago. You can hear the vibrant proclamations of “we outside” and folks runnin’ it up on Resy. And if you know me, I LIVE for a great meal and reco’s are my thing. Plus, I’d argue that Chicago has some of the best food in the country--bar none. If you’re new here, check out my Part 1 blog post featuring 17 Chicago restaurants to try.

From brunch to date night, below are 12 restaurants throughout the Chicagoland area worth trying:

Day & Night

Maple & Ash

8 W. Maple St, Chicago, IL

If you're in the mood for an upscale brunch, go to Maple & Ash. If you're in the mood for an exclusive dining experience, go to Maple & Ash. Long story short, I'm a fan and repeat visitor of this delicious steak and seafood restaurant in Chicago's Gold Coast neighborhood. The fare here is fantastic, and the ambiance gives luxe. The menu is crafted by two-Michelin-star Chef Danny Grant, and they even have a menu item called "I Don't Give a F*@ck," a $200-per-person order aimed at big spenders.

Siena Tavern

51 W Kinzie St, Chicago, IL

This spacious, modern Italian restaurant in River North Chicago serves classic Italian fare like homemade pasta and Coccoli. The bar is a vibe, and so is the main dining area, so it's a great spot for happy hour or lunch. I love their specialty cocktail No. 2, and I will never NOT order the Burrata or Gnocchi from here. They're my faves.

Siena Tavern Chicago



1421 W Chicago Ave, Chicago, IL

This space is small but the food packs quite a delicious punch. Provare serves Creole + Italian fusion with offerings like shrimp Hennessey scampi, fried lobster tails, and salmon egg rolls. I guarantee their IG pics will make your tastebuds anxious with anticipation. Reservations require a $5 deposit per person to be applied toward your bill.

Frances Brunchery

2552 N Clark St, Chicago, IL

This diner/deli transformed into a Brunchery is definitely a place to try amongst the rest of the brunch scene. From specialty French toast to various “eggs-quisite” dishes, they have a wide array of breakfast and brunch options for every palette. What I love most is the rotating specialty menu.

Frances Brunchery Chicago

Casual Brunch


1055 E 55th St, Chicago, IL

I almost wanted to gatekeep this one, but sharing is caring. Gaining in popularity, Roux is a New Orleans and Southern-inspired spot in the Hyde Park neighborhood. You order at the counter, find a seat with a table number and wait for your food to be delivered. My go-to's are the shrimp & grits, and cinnamon roll (to die for). But be warned, they don't take reservations based on the format and could run out of certain items if it's poppin and you get there late.

Wake N Bacon

420 W Belmont Ave, Chicago, IL

If you google “best Instagrammable brunch Chicago” this place comes up. The menu offers American, Asian, and Latin flavors. The Ube Flap Jack Stack and the Turtle Waffle were delicious. The interior is chic and decked out with hanging flowers. They also aim “high” to please, offering CBD upgrades to your food and drink if that’s your jam.

Central & South American Cuisine


652 W Randolph St, Chicago, IL

I went here for my birthday, and it indeed was an experience! Aikana is beautifully decorated, and feels like you've been transported to a South American getaway. The presentation of the handcrafted cocktails and food menu is incredible and aims to evoke luxury. This is a special occasion place if you're looking for something different and new.

El Che

845 W Washington Blvd, Chicago, IL

El Che brings wood-fired Argentinean-American & South American fare and cocktails to the city. The vibe is cozy, and the staff was super friendly (from the hostess to the bartender to our waiter - seriously). My girls and I shared the Grilled Shellfish Parrillada, which was SO good! The sauce?! Disrespectful. My mid picture does not do it justice.

El Che Chicago

Upscale Mexican + American Flare


720 N State St, Chicago, IL

You'll be instantly transported to Mexico when you step through the doors of Tzuco. A concept by Michelin star Chef Carlos Gaytan, the space is gorgeously decorated with warm, earthy tones and imported ceramics. Even the bathroom is an experience. My faves were the Papas Zamoranas and Gianduja.


65 W Kinzie St, Chicago, IL

Located in the heart of River North with its rustic-industrial decor, Barrio is a great, after-work option with its shared-plate format. What's great is they also have options for those who eat organic and are gluten-free. The happy hour menu has excellent options, and the elotes do not disappoint.

Bougie Brunch

3 Arts Club Cafe (in Restoration Hardware)

1300 N Dearborn St, Chicago, IL

I included this spot in my Chicago date night ideas blog post but had to spin the block. Located in Restoration Hardware, this spot (plus the location in Oak Brook) is growing in popularity with the IG girlies. If you're looking for a bougie, posh brunch with friends, or bae, you'll get it at 3 Arts Club. I thoroughly enjoyed the ambiance, burger, and shaved ribeye on charred garlic bread - magnifique!

Food Hall

Time Out Market

916 W Fulton Market, Chicago, IL

This is the perfect place for some who don't know what they actually want to eat. From soul food to sushi to sweets, Time Out Market Chicago is a curated food hall that doesn't disappoint. It has some of the highest-rated local restaurants in Chicago, all under one roof. I personally enjoyed the ramen from Urbanbelly.

Time Out Market Chicago

Vibe Dining


5121 S Harper Ave. Chicago, IL

Chemistry Chicago has a very vibrant atmosphere and flavorful food. Between the sparklers, live band, and DJ, this spot is lit. In other words, plan to show up to have a good time, not hold an intimate conversation (it's relatively loud). The menu is intentional and fun, with each category named after a phase in the dating and/or relationship journey (e.g., the dating phase, the engagement, meet the family, etc.). Although the menu is on the pricier side, IMO, the airline chicken and truffle Alfredo fries were a hit!

What spots are you looking forward to trying? Let me know in the comment section below or on IG @andthatsjustashley

Let's eat!

285 views0 comments

Recent Posts

See All


bottom of page